A general synthesis of long chain ω- and (ω-1)-hydroxy fatty acids

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DOIResolve DOI: http://doi.org/10.1016/0009-3084(81)90023-2
AuthorSearch for:
TypeArticle
Journal titleChemistry and Physics of Lipids
ISSN0009-3084
Volume28
Issue4
Pages379384; # of pages: 6
AbstractA method for the synthesis of long chain fatty acids substituted at the ω and ω-1 positions has been developed. The key step is the isomerization of the triple bond of an alkyn-1-ol from an internal position in the chain to the free terminus with a new, convenient reagent, sodium aminopropylamide (NaAPA). Standard functional group manipulations i.e., Jones oxidation, esterification and hydroboration of the triple bond are used to prepare ω-hydroxy fatty esters. The generality of the method is illustrated with syntheses of ω-hydroxy fatty esters with 24, 26, 28 and 30 carbon chains. In the 24 carbon series, hydration of the terminal triple bond of alkynoic ester 4a followed by reduction gave the (ω-1)-hydroxy ester.
Publication date
LanguageEnglish
AffiliationNRC Plant Biotechnology Institute; National Research Council Canada
Peer reviewedYes
NRC number19103
NPARC number21273760
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Record identifier870eda76-fd6b-4f18-9305-1d177db95942
Record created2015-01-20
Record modified2016-05-09
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